Great question @vmwauto01!
Our Square Invoice feature will allow you to download every paid invoice as a PDF file. However, there is no way to send out all of them at once or add them up. Unless you manually download one by one and send it via your email, this is a feature request that we yet don't have available.
Hope this helps!
Sayra
Community Moderator, Square // Moderadora de la Comunidad, Square
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